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Revision as of 14:11, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,045 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit		Latest revision as of 23:09, 9 February 2024 edit undoMichael7604 (talk | contribs)Extended confirmed users8,895 edits is an aryl iodide
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	{{chembox		{{chembox
			|Watchedfields = changed
	| verifiedrevid = 414427617		|verifiedrevid = 443876350
	| Name = Iodobenzene
	| ImageFileL1 = Iodbenzol.svg		|Name = Iodobenzene
			|ImageFileL1 = Iodbenzol.svg
	| ImageSizeL1 = 80px		|ImageSizeL1 = 80px
	| ImageNameL1 = Iodobenzene		|ImageNameL1 = Iodobenzene
	| ImageFileR1 = Iodobenzene-3D-vdW.png		|ImageFileR1 = Iodobenzene-3D-vdW.png
	| ImageSizeR1 = 120px		|ImageSizeR1 = 120px
	| ImageName1 = Space-filling model of iodobenzene		|ImageName1 = Space-filling model of iodobenzene
	| IUPACName = Iodobenzene		|PIN = Iodobenzene
	|OtherNames = Phenyl iodide		|OtherNames = Phenyl iodide
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 11087		|ChemSpiderID = 11087
	| PubChem = 11575		|PubChem = 11575
	| InChI = 1/C6H5I/c7-6-4-2-1-3-5-6/h1-5H		|InChI = 1/C6H5I/c7-6-4-2-1-3-5-6/h1-5H
	| InChIKey = SNHMUERNLJLMHN-UHFFFAOYAQ		|InChIKey = SNHMUERNLJLMHN-UHFFFAOYAQ
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 116296		|ChEMBL = 116296
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H		|StdInChI = 1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = SNHMUERNLJLMHN-UHFFFAOYSA-N		|StdInChIKey = SNHMUERNLJLMHN-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		|CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 591-50-4		|CASNo = 591-50-4
			|UNII_Ref = {{fdacite|correct|FDA}}
⚫	| DrugBank = DB02252
			|UNII = 9HK5L7YBBR
⚫	| SMILES = c1ccc(cc1)I
			|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
		⚫	|DrugBank = DB02252
		⚫	|SMILES = c1ccc(cc1)I
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>6</sub>H<sub>5</sub>I		|Formula = C<sub>6</sub>H<sub>5</sub>I
			|Appearance = colorless liquid
	| MolarMass = 204.01 g/mol
	| Density = 1.831 g/cm<sup>3</sup>		|MolarMass = 204.01 g/mol
			|Density = 1.823 g/cm<sup>3</sup>
	| MeltingPt = −29 °C
			|MeltingPtC = −29
	| BoilingPt = 188 °C
			|BoilingPtC = 188
			|LogP = 3
			|Solubility = Insoluble
			|MagSus = -92.00·10<sup>−6</sup> cm<sup>3</sup>/mol
			|Viscosity = 1.5042 mPa·s (300.65 K)<ref>{{Citation|last1=Viswanath|first1=D.S.|last2=Natarajan|first2=G.|title=Data Book on the Viscosity of Liquids|publisher=Hemisphere Publishing|year=1989|isbn=0-89116-778-1}}</ref>
		⚫	}}
			|Section3={{Chembox Hazards
			|FlashPtC = 74.44
			}}
			|Section4={{Chembox Thermochemistry
			|HeatCapacity = 0.779 J/K
			}}
			|Section9={{Chembox Related
			| OtherFunction_label = halobenzenes
			| OtherFunction = ]<br />]<br />]
	}}		}}
	}}		}}
	'''Iodobenzene''' is an ] consisting of a ] ring substitituted with one ] atom. It is useful as a synthetic intermediate in ].		'''Iodobenzene''' is an ] and the simplest of the ], consisting of a ] ring substituted with one ] atom. Its chemical formula is {{chem2|C6H5I}}. It is useful as a synthetic intermediate in ]. It is a volatile colorless liquid, although aged samples appear yellowish.
	==Preparation==		==Preparation==
	Iodobenzene is commercially available, but it may be prepared in the laboratory from ] via the ]. In the first step, the ] functional group is ] with ] and ]. ] is added to the resultant diazonium chloride, causing ] gas to evolve. Any excess nitrite is hydrolyzed with a strong base; the mixture is acidified and the desired product is separated by steam distillation.<ref>{{OrgSynth		Iodobenzene is commercially available, or it can be prepared in the laboratory from ] via the diazotization reaction. In the first step, the ] functional group is ] with ] and ]. ] is added to the resultant ], causing ] gas to evolve. The product is separated by steam distillation.<ref name=Lucas>{{OrgSynth
	| author = H. J. Lucas, E. R. Kennedy		| author = H. J. Lucas, E. R. Kennedy
	| title = Iodobenzene		| title = Iodobenzene
	| year= 1939		| year = 1939
	| collvol = 2		| collvol = 2
	| collvolpages = 351		| collvolpages = 351
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	:]		:]
	Alternatively, it may be produced by refluxing ] and ] with benzene.<ref>{{OrgSynth		Alternatively, it can be produced by refluxing ] and ] with benzene.<ref>{{OrgSynth| author = F. B. Dains and R. Q. Brewster| title = Iodobenzene| year = 1941| collvol = 1| collvolpages = 323| prep = cv1p0323}}</ref>
	| author = F. B. Dains and R. Q. Brewster
	| title = Iodobenzene
	| year= 1941
	| collvol = 1
	| collvolpages = 323
	| prep = cv1p0323
⚫	}}
	</ref>
	==Reactions==		==Reactions==
	Since the C–I bond is weaker than C–Br or C–Cl, iodobenzene is more reactive than ] or ]. Iodobenzene can react with ] to form the ], phenylmagnesium iodide. Phenylmagnesium iodide, like the ], is a synthetic equivalent for the ] anion ]. Iodobenzene reacts with chlorine to give the complex, ],<ref>{{OrgSynth | title = Iodobenzene dichloride | author = H. J. Lucas and E. R. Kennedy | prep = cv3p0482 | collvol = 3 | collvolpages = 482}}</ref> which is used as an oxidant.		Since the C–I bond is weaker than C–Br or C–Cl, iodobenzene is more reactive than ] or ]. Iodobenzene reacts readily with ] to form the ], phenylmagnesium iodide. Phenylmagnesium iodide, like the ], is a synthetic equivalent for the ] anion ]. Iodobenzene reacts with chlorine to give the complex, ],<ref>{{OrgSynth | title = Iodobenzene dichloride | author = H. J. Lucas and E. R. Kennedy | prep = cv3p0482 | collvol = 3 | collvolpages = 482}}</ref> which is used as a solid source of chlorine.
	Iodobenzene can also serve as a ] for the ], ], and other metal-catalyzed couplings.		Iodobenzene can also serve as a ] for the ], ], and other metal-catalyzed couplings. These reactions proceed via the ] of iodobenzene.
⚫	==References==
⚫	<references/>
	==Further reading==		==Further reading==
	*Gattermann-Wieland, "Laboratory Methods of Organic Chemistry," p. 283. Translated from the twenty-fourth German edition by W. McCartney, The Macmillan Company, New York, 1937.		*Gattermann-Wieland, "Laboratory Methods of Organic Chemistry," p. 283. Translated from the twenty-fourth German edition by W. McCartney, The Macmillan Company, New York, 1937.
		⚫	==References==
⚫	]
		⚫	<references/>
⚫	]
		⚫	]
	]
		⚫	]
	]
	]
	]
	]
	]